p-Toluidine → 3-Pyridinamine, N-(4-methylphenyl)-

HRID 741316Notes

Reaction equation

HRID 741316 reaction equation
Cc1ccc(N)cc1.Ic1cccnc1>CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C.COC(=O)c1cc(-c2cccs2)on1.COc1ccc(OC)c([P](C(C)(C)C)(C(C)(C)C)->[Pd]2(<-[NH2]c3ccccc3-c3cccc[c]32)[O]S(=O)(=O)C(F)(F)F)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(C)=O>Cc1ccc(Nc2cccnc2)cc1

Participants

7

Reactant 2

HCID 7813p-ToluidineHCID 707143-Iodopyridine

Product 1

HCID 6035893-Pyridinamine, N-(4-methylphenyl)-Yield 50.405%

Reagents, catalysts & solvents 4

HCID 1256578methyl 5-(2-thienyl)isoxazole-3-carboxylateReagentHCID 33931062,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramineReagentHCID 178492620HCID 178492620, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

Conditions

Temperature
60 °C

Procedure

These solutions were added to a 384- well source plate (80 µL per well). The Mosquito HTS liquid handling robot was used to dose each of these solutions (200 nL each) into a 1536-well plate.

Workup

  1. additionNo procedure recorded

Sources & evidence

ORD record
ord-89c39ced5b1d455789a89af61ca3633e
Source dataset
Ahneman

Reaction notes

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